Lot numbers can be found on the outside label of a product:
2',3'-O-Isopropylideneadenosine
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CAS No. 362-75-4
- Cat. No. CS-W008048
- Purity≥98%
- MDL No.MFCD00005756
*For research and further manufacturing use only, not for direct human use.
Structure of 362-75-4
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General Information
- CAS No. 362-75-4
- Cat. No. CS-W008048
- Purity ≥98%
- MDL No. MFCD00005756
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₃H₁₇N₅O₄
- Molecular Weight 307.31
- Synonym(s) 2,3-O-Isopropylideneadenosine
- SMILES NC1=NC=NC2=C1N=CN2[C@H]3[C@H]4[C@H](OC(C)(C)O4)[C@@H](CO)O3
Description
2',3'-O-Isopropylideneadenosine features a protected ribose moiety that enhances stability during nucleoside synthesis and purification. The isopropylidene group selectively masks the 2' and 3' hydroxyls, enabling efficient orthogonal protection in carbohydrate-directed reactions. This derivative simplifies downstream modifications in oligonucleotide assembly and facilitates handling under standard bench conditions.
Application
2',3'-O-Isopropylideneadenosine serves as a key protected nucleoside intermediate in oligonucleotide synthesis and carbohydrate chemistry. The isopropylidene acetal selectively protects the 2' and 3' hydroxyl groups of adenosine, offering enhanced stability during acidic conditions and facilitating orthogonal deprotection workflows. Its bench-stable nature and compatibility with standard coupling protocols make it a practical choice for building complex glycosylated scaffolds and modified nucleosides in medicinal chemistry applications.
Synthesis
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Route1
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77-76-9 -
58-61-7 - ~93%
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In-stock
362-75-4
References
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INSPIRE PHARMACEUTICALS, INC. Patent: WO2005/39590 A1, 2005 ; Location in patent: Page/Page column 53 ; WO 2005/039590 A1
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Route2
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67-64-1
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58-61-7
- ~99%
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In-stock
362-75-4
References
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Devkota, Kanchan; Lohse, Brian; Liu, Qing; Wang, Ming-Wei; Staerk, Dan; Berthelsen, Jens; Clausen, Rasmus Praetorius ACS Medicinal Chemistry Letters, 2014 , vol. 5, # 4 p. 293 - 297
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Route3
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29706-75-0
- ~95%
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In-stock
362-75-4
References
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Vincent, Stephane; Mioskowski, Charles; Lebeau, Luc Journal of Organic Chemistry, 1999 , vol. 64, # 3 p. 991 - 997
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 117.54
- LogP -0.1817
- H_Acceptors 9
- H_Donors 2
- Rotatable_Bonds 2
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Key Words
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